The Exchanges

Q not on schedule, but fuck it. I told you I'm not a sounder journalist, but you mentioned your parents there in the upbringing. I think parents impact you so much more than, than one thinks. When you look back to your parents, seeing their work ethic, and growing up really in that household, like, how do you think that impacted your mindset, and what were some big takeaways for you?

A So my parents worked very, very hard to put food on the table. Just to give you a sense, I've had two jobs since I graduated college. I worked at McKinsey, and I've been at Insight. Between being 11 in that McKinsey job, I held 19 different jobs. So I've done everything to pay the bills. So they instilled this notion that if I wanted something, I'd have to go get it, and that hard work was okay. That was the clear message that they showed through their efforts. You know, ingenuity and hard work would pay off, and that's what they did. And they were highly supportive relative to whatever I wanted to do. What they didn't do, because they didn't know, they didn't pay the way and say, you need to go to an Ivy League college, or you need to do this or that. They had no idea. You know, if it was up to my dad, I would have been an actuary. Funny story. So the only business profession he knew is he worked for one guy, and he had this huge house, and it was, he was an actuary. He ran, like, the American Actuarial Society, and it was a really nice house. So my dad, when I went to Penn, was like, you got to become an actuary. They have a great actuarial science program there. If you know me, like, that would probably be the worst profession ever for me. I would have, like, failed out. So I took one actuary class, and it was awful. I dropped it after about a month, thankfully, but that was…

AI assessment note: “they instilled this notion that if I wanted something, I'd have to go get it”

Q not on schedule, but fuck it. I told you I'm not a sounder journalist, but you mentioned your parents there in the upbringing. I think parents impact you so much more than, than one thinks. When you look back to your parents, seeing their work ethic, and growing up really in that household, like, how do you think that impacted your mindset, and what were some big takeaways for you?

A So my parents worked very, very hard to put food on the table. Just to give you a sense, I've had two jobs since I graduated college. I worked at McKinsey, and I've been at Insight. Between being 11 in that McKinsey job, I held 19 different jobs. So I've done everything to pay the bills. So they instilled this notion that if I wanted something, I'd have to go get it, and that hard work was okay. That was the clear message that they showed through their efforts. You know, ingenuity and hard work would pay off, and that's what they did. And they were highly supportive relative to whatever I wanted to do. What they didn't do, because they didn't know, they didn't pay the way and say, you need to go to an Ivy League college, or you need to do this or that. They had no idea. You know, if it was up to my dad, I would have been an actuary. Funny story. So the only business profession he knew is he worked for one guy, and he had this huge house, and it was, he was an actuary. He ran, like, the American Actuarial Society, and it was a really nice house. So my dad, when I went to Penn, was like, you got to become an actuary. They have a great actuarial science program there. If you know me, like, that would probably be the worst profession ever for me. I would have, like, failed out. So I took one actuary class, and it was awful. I dropped it after about a month, thankfully, but that was…

AI assessment note: “they instilled this notion that if I wanted something, I'd have to go get it”

Q Did this change your process when you reflect on that? Have you changed the result?

A Yes, absolutely. So when I came in from McKinsey, I had this notion that a whiteboard and a pen coming out of McKinsey, I could solve any problem in the world, right? I was this arrogant, twenty-two-year-old. I made a lot of top-down, hypothesis-driven investments. And I quickly realized when kind of the water receded that there was nothing there. And my hypothesis, although not wrong, were massively off from a timing standpoint and a viability standpoint. I lost a lot of money, like a ton of money. So it was a very, very painful period. So I quickly reverted to the opposite and say, well, let me actually start bottoms up finding companies that are actually concretely solid with real unit economics and that are real. And I'm going to ignore all the story. And I made some investments, call it in the O two to O five Timeframe, which did pretty well, but none of them were breakout successes. You know, I realized with the Shutterstock experience and some other experiences that it really needed to be this high, low, top-down, bottom-up toggle that you need to keep doing, and that one is not right and the other's not wrong. They're both right. It's kind of the notion of being comfortable with an and. I am top-down and I am bottom-up versus one versus the other. You know, I iterate now a lot with this notion of, like, I want to see some really, really good trends within the company, b…

AI assessment note: “Yes, absolutely. So when I came in from McKinsey, I had this notion”

Q know, you mentioned your entry there into Insight and into the world of venture. I'm always very cognizant. I've never experienced a downturn. I've Suddenly experienced a boom in the last few years, but I've never experienced a downturn. You've seen multiple booms and busts. How did seeing the multiple booms and busts, how did that impact your investing mindset? And I guess, like, advising me, what should I know?

A You know what, what I would say is, I mean, I started doing this earnestly in 98. We made a lot of investments. I led a lot of investments, and that's part of Insight's process to let young people do lots of stuff. And for a good two years, you know, I was on top of the world. I was a genius. Everything was marked up. I looked fantastic. As did all our, you know, the peers at Insight and peers across the industry. Come on one, what was great beyond great becomes, you know, awful, and you live through a period of pain with restructuring, termination, writing things down, writing things off. The high was high, the low was low. You know, I think the biggest lesson is that you got to moderate your point of view on the ups, and you got to moderate your point of views on the down. It's probably never as bad as it looks, probably never as good as it looks. You look at the last year, what we had, you know, 50% returns I read this weekend across the industry. Like, as an industry, that's ridiculous. Massively unsustainable. We're not all that smart. We're not all that good, including myself. It's not possible. So there's clearly something going on, and there'll be some amount of mean reversion, whether the mean shoots to the opposite side of way below that, who knows? But number one lesson is you got to moderate the ups. You got to moderate the downs. 2001 dip versus the oh eight dip, v…

AI assessment note: “number one lesson is you got to moderate your point of view on the ups”

Q I actually spoke to one of your younger team members, and they said that you recently told them when they had a company that was struggling, like, you know, is nature of our business, that actually to learn in this business, you have to lose money. Can you unpack that for me and that learning process in venture and what you meant by to learn you have to lose money?

A Let me start with, I hate losing money. I hate, hate, hate losing money. I feel it. I don't sleep well. So like it definitely gets to you. So I'll start with that. You know, when I started in this business, we had a large competitor. I won't name. They're still around. They had this mantra I interviewed with them that they had never lost money. And it was a badge of honor that they had never lost money on investment. And I thought it was great right at the time. I was like, oh, that's amazing. Like how Perfect. Are they? And the reality is in our business, like we can set a bet and ultimately at the end of the day, whether or not that bet pays off at a certain level, it's out of our control. We control lots of things, but things break good. They break bad. Things happen. It's a messy process. So you have to live in a world where you're accepting of failure in the face of that failure. You start to really look at and examine your assumptions, your truths, everything works. You just think you're a genius. When things start Stop working. Then you start questioning your assumptions, and when you start questioning your assumptions, I think that's where the real learning begins. There's lots of, you know, psychological writing on this, but, you know, I think in the suffering, that is where the truth is, and I do fundamentally believe that. I think it's much, much easier to learn from…

AI assessment note: “when you start questioning your assumptions, I think that's where the real learning begins.”

Q know, you mentioned your entry there into Insight and into the world of venture. I'm always very cognizant. I've never experienced a downturn. I've Suddenly experienced a boom in the last few years, but I've never experienced a downturn. You've seen multiple booms and busts. How did seeing the multiple booms and busts, how did that impact your investing mindset? And I guess, like, advising me, what should I know?

A You know what, what I would say is, I mean, I started doing this earnestly in 98. We made a lot of investments. I led a lot of investments, and that's part of Insight's process to let young people do lots of stuff. And for a good two years, you know, I was on top of the world. I was a genius. Everything was marked up. I looked fantastic. As did all our, you know, the peers at Insight and peers across the industry. Come on one, what was great beyond great becomes, you know, awful, and you live through a period of pain with restructuring, termination, writing things down, writing things off. The high was high, the low was low. You know, I think the biggest lesson is that you got to moderate your point of view on the ups, and you got to moderate your point of views on the down. It's probably never as bad as it looks, probably never as good as it looks. You look at the last year, what we had, you know, 50% returns I read this weekend across the industry. Like, as an industry, that's ridiculous. Massively unsustainable. We're not all that smart. We're not all that good, including myself. It's not possible. So there's clearly something going on, and there'll be some amount of mean reversion, whether the mean shoots to the opposite side of way below that, who knows? But number one lesson is you got to moderate the ups. You got to moderate the downs. 2001 dip versus the oh eight dip, v…

AI assessment note: “biggest lesson is that you got to moderate your point of view on the ups”

Q that actually, I've learned the most from the misses that I've had, and I've had, despite the short time, Jeff, quite a few. I mean, stellar misses. My question to you, and it's really changed my process and how I think about companies a lot. If you were to choose one or two of your biggest misses, what are they, and how did it change how you think about investing?

A When I think about misses, we look at everything in Insight, right? So we've missed basically everything that's big out there. A slight exaggeration, but not far from the truth. As a firm, we've missed it all. Any big company has probably been touched by Insight, and there's some failure amongst us collectively to have identified it as a trend. Where I'd beat myself up if I was going to beat myself up, and I try not to. We were really early on photography, so I invested in a company called Shutterstock, which we took public. We were the first investors that, like, it was a five million dollar company at the time. Fantastic business, Stock photography, and the investment thesis was that pictures, both still and videos, this is 15 years ago, 2000 five-ish time frame, so 17 years ago, they were going to change the world, and the internet was going to enable these to move very fast across networks and people. It just pains me that I didn't take it to the logical next step relative to all these social networks like Instagram and Snapchat and other things that are driven by video and by photos, and it's in the Shutterstock stuff. I wrote it, That physical representation was just such a better way, the notion of a photo was such a better way to express emotion and communicate than the written word, yet I didn't take it to the logical final.

AI assessment note: “It just pains me that I didn't take it to the logical next step”

Q I actually spoke to one of your younger team members, and they said that you recently told them when they had a company that was struggling, like, you know, is nature of our business, that actually to learn in this business, you have to lose money. Can you unpack that for me and that learning process in venture and what you meant by to learn you have to lose money?

A Let me start with, I hate losing money. I hate, hate, hate losing money. I feel it. I don't sleep well. So like it definitely gets to you. So I'll start with that. You know, when I started in this business, we had a large competitor. I won't name. They're still around. They had this mantra I interviewed with them that they had never lost money. And it was a badge of honor that they had never lost money on investment. And I thought it was great right at the time. I was like, oh, that's amazing. Like how Perfect. Are they? And the reality is in our business, like we can set a bet and ultimately at the end of the day, whether or not that bet pays off at a certain level, it's out of our control. We control lots of things, but things break good. They break bad. Things happen. It's a messy process. So you have to live in a world where you're accepting of failure in the face of that failure. You start to really look at and examine your assumptions, your truths, everything works. You just think you're a genius. When things start Stop working. Then you start questioning your assumptions, and when you start questioning your assumptions, I think that's where the real learning begins. There's lots of, you know, psychological writing on this, but, you know, I think in the suffering, that is where the truth is, and I do fundamentally believe that. I think it's much, much easier to learn from…

AI assessment note: “when you start questioning your assumptions, I think that's where the real learning begins.”

Q My interviewing has made me a better investor. For sure. A hundred percent. You know, everyone changes leadership styles over time, and now, you know, you've been sitting in a leadership seat for many years. How has your leadership style changed over the years? You mentioned interactions there with analysts and other team members. How has your own leadership style changed?

A Like I said earlier, I was kind of in a do mode coming out of college, so let's call it the first 10 years of my career. It was all about investing. I was very instinctual. I was very deeply felt and just did, but I didn't articulate Particulate the whys. I mean, I would say over the last 10 or 15 years, I've moved to a much more intentional model relative to this, why do I do the things I do, and then prescriptively think through what I want to achieve, and then figure out how I'll achieve that, and that's really about how I manage people, because at the end of the day, I wasn't trained at a company to manage people, so it's all very intentional relative to, these are the types of things we need to do to achieve the goals that we want to achieve, so there's a deep intentionality that increased over the years, for sure, from nothing, literally.

AI assessment note: “over the last 10 or 15 years, I've moved to a much more intentional model”

Q Did this change your process when you reflect on that? Have you changed the result?

A Yes, absolutely. So when I came in from McKinsey, I had this notion that a whiteboard and a pen coming out of McKinsey, I could solve any problem in the world, right? I was this arrogant, twenty-two-year-old. I made a lot of top-down, hypothesis-driven investments. And I quickly realized when kind of the water receded that there was nothing there. And my hypothesis, although not wrong, were massively off from a timing standpoint and a viability standpoint. I lost a lot of money, like a ton of money. So it was a very, very painful period. So I quickly reverted to the opposite and say, well, let me actually start bottoms up finding companies that are actually concretely solid with real unit economics and that are real. And I'm going to ignore all the story. And I made some investments, call it in the O two to O five Timeframe, which did pretty well, but none of them were breakout successes. You know, I realized with the Shutterstock experience and some other experiences that it really needed to be this high, low, top-down, bottom-up toggle that you need to keep doing, and that one is not right and the other's not wrong. They're both right. It's kind of the notion of being comfortable with an and. I am top-down and I am bottom-up versus one versus the other. You know, I iterate now a lot with this notion of, like, I want to see some really, really good trends within the company, b…

AI assessment note: “Yes, absolutely. So when I came in from McKinsey, I had this notion”

Q But what do you think you do to train them in a way that others don't to make them so good?

A We flipped the notion of investing in venture capital on its head, so if you look back 25 years ago, there weren't Junior people in venture capital is a bunch of senior people. I mean, I got rejected by every one of those senior people, and I sent them resumes from Penn. They didn't take junior people. You needed operating experience. What we did was we said, no, there's a role for junior people. In fact, in a world that's decentralized, in a world that's global, in a world that's innovating very quickly, you need to hire super, super smart, super energetic, super passionate, inquisitive people to go find really interesting stuff, and if it's Command and control and on the bottleneck, we're going to be outdated very quickly. That is the start of kind of the culture and the idea, and that's what we did at the beginning, and we institutionalized that. If you think about learning in general, a very, very simplistic framework, you know, at the one extreme, you have educational institutions, classroom learning, and at the other extreme, you have doing. I would argue in our business, and in most business, classrooms don't work. I mean, I took marketing classes. You know, most Business classes aren't practical relative to what it is to be a VC. I mean, I've taught classes at Columbia and Penn and other places on VC, and it's a hard thing to teach. Like, how do you teach a young person…

AI assessment note: “The Insight approach is all about giving young people actual experience”

Q Not at all. I've been wanting to do this one for a long time, but I do want to start with a little bit on you and a bit of the story. 24 years now with Insight, so how did you make your way into the world of Venture, and what was that entry for you?

A Yeah, my story starts, I grew up in Jersey, which I'm in New York City, so it's about 20 miles across the river. My dad's a union electrician. My mom did odd jobs growing up. Neither of my parents graduated college, so we didn't have a lot of money. Total working class. And if you asked me, you know, what venture capital was when I was a teenager, I would have looked at you with a blank, you know, stare in my face. What I did growing up to make some money is work with my dad. So on the weekends and after school, I was his helper. And I'm a small little guy. What that usually meant was I was digging ditches to run wire or working my way through attics pulling wire. And what you learn, and it was probably the number one first life lesson I got, was manual labor isn't fun. I mean, I learned that like the hard way because I was doing it. And I quickly realized I wanted to use my brain, not my brawn, although I didn't have much brawn, to make a living. I started thinking about what do you do to use your brain? My dad's friends were electricians and plumbers and carpenters, so I didn't really know people that had done business or done highly intellectual things. So to me, I had this very narrow set. It was pre-internet. I was either going to be a lawyer, a doctor, or a business person. I didn't like the law shows on TV, so that was out. Doctoring, I was afraid of blood, so that was o…

AI assessment note: “I quickly realized I wanted to use my brain, not my brawn”

Q You said they didn't, like, you know, push you, like, a lot of maybe more modern helicopters Parents might push their children as we see and hear about. Do you wish he had pushed you more? And I guess with your children today, is it right to push them, or is it right to let them find their own path, or do they need guidance? Help me out.

A The intrinsic motivation I had was there was scarcity mentality in my household, because like my dad, he's a union electrician, so, you know, after a job, you can get laid off, and you're not working for a month or two or whatever, so there was always this fear that he wouldn't have a paycheck, so my mom was always doing some odd job, and he was always doing some odd job, and we were always Trying to, you know, scrimp on money. I always grew up with this scarcity mentality, which has taken a long time over the years to change, so there's a lot of intrinsic motivation to work, so I never had that problem. Intrinsically, there's something about, like, excellence that I'm just attracted to, so that was just this notion of, like, well, how do we do something great? That's just something intrinsic. With my kids, you know, fast forward, I got two teenagers, you know, I joke with my wife, and I'm like, well, I don't, I don't really care if they go to college or not. Now, Penn, as I just told you, was this huge elevator for me. My kids kind of have that elevator already. I want them to, you know, Excited by, that they're productive by, that they can intrinsically just get up every day and, like, be motivated to do something productive for society, so we don't push very hard. They have huge opportunities. They have huge advantage. They have huge privilege, and if they go to Penn, that's…

AI assessment note: “so we don't push very hard. They have huge opportunities.”

Q that actually, I've learned the most from the misses that I've had, and I've had, despite the short time, Jeff, quite a few. I mean, stellar misses. My question to you, and it's really changed my process and how I think about companies a lot. If you were to choose one or two of your biggest misses, what are they, and how did it change how you think about investing?

A When I think about misses, we look at everything in Insight, right? So we've missed basically everything that's big out there. A slight exaggeration, but not far from the truth. As a firm, we've missed it all. Any big company has probably been touched by Insight, and there's some failure amongst us collectively to have identified it as a trend. Where I'd beat myself up if I was going to beat myself up, and I try not to. We were really early on photography, so I invested in a company called Shutterstock, which we took public. We were the first investors that, like, it was a five million dollar company at the time. Fantastic business, Stock photography, and the investment thesis was that pictures, both still and videos, this is 15 years ago, 2000 five-ish time frame, so 17 years ago, they were going to change the world, and the internet was going to enable these to move very fast across networks and people. It just pains me that I didn't take it to the logical next step relative to all these social networks like Instagram and Snapchat and other things that are driven by video and by photos, and it's in the Shutterstock stuff. I wrote it, That physical representation was just such a better way, the notion of a photo was such a better way to express emotion and communicate than the written word, yet I didn't take it to the logical final.

AI assessment note: “it just pains me that I didn't take it to the logical next step”

Q You said they didn't, like, you know, push you, like, a lot of maybe more modern helicopters Parents might push their children as we see and hear about. Do you wish he had pushed you more? And I guess with your children today, is it right to push them, or is it right to let them find their own path, or do they need guidance? Help me out.

A The intrinsic motivation I had was there was scarcity mentality in my household, because like my dad, he's a union electrician, so, you know, after a job, you can get laid off, and you're not working for a month or two or whatever, so there was always this fear that he wouldn't have a paycheck, so my mom was always doing some odd job, and he was always doing some odd job, and we were always Trying to, you know, scrimp on money. I always grew up with this scarcity mentality, which has taken a long time over the years to change, so there's a lot of intrinsic motivation to work, so I never had that problem. Intrinsically, there's something about, like, excellence that I'm just attracted to, so that was just this notion of, like, well, how do we do something great? That's just something intrinsic. With my kids, you know, fast forward, I got two teenagers, you know, I joke with my wife, and I'm like, well, I don't, I don't really care if they go to college or not. Now, Penn, as I just told you, was this huge elevator for me. My kids kind of have that elevator already. I want them to, you know, Excited by, that they're productive by, that they can intrinsically just get up every day and, like, be motivated to do something productive for society, so we don't push very hard. They have huge opportunities. They have huge advantage. They have huge privilege, and if they go to Penn, that's…

AI assessment note: “so we don't push very hard. They have huge opportunities. They have huge advantage.”

Q purely on the investing side, but it's, it's crucial to everything that we do. It's firm building. It's probably the most challenging of all. 24 years now, you've been in many different positions within Insight, and, you know, for the last several years, been building the firm as one of the leaders. What are some of the biggest challenges of firm building, do you think, from your time building Insight?

A Yeah, you know, we've gone from when I started, there was a couple of us, and, you know, now we have hundreds. So it's all about the people. I think the mission and uniqueness of Insight is we have created an organization, a culture, and a platform that takes very, very talented young people and turns them into world-class software investors and investors And I think that's what we do. I think uniquely well at scale and have done that. So I think our biggest challenge and our biggest opportunity and our biggest differentiation is to continue to do that well. And as you get bigger and bigger, we have amazing ingredients, but we're taking really, really talented young people. And then literally within two to five years, we have these amazing investors and that are literally world-class.

AI assessment note: “our biggest challenge and our biggest opportunity and our biggest differentiation is to continue to do that well”

Q My interviewing has made me a better investor. For sure. A hundred percent. You know, everyone changes leadership styles over time, and now, you know, you've been sitting in a leadership seat for many years. How has your leadership style changed over the years? You mentioned interactions there with analysts and other team members. How has your own leadership style changed?

A Like I said earlier, I was kind of in a do mode coming out of college, so let's call it the first 10 years of my career. It was all about investing. I was very instinctual. I was very deeply felt and just did, but I didn't articulate Particulate the whys. I mean, I would say over the last 10 or 15 years, I've moved to a much more intentional model relative to this, why do I do the things I do, and then prescriptively think through what I want to achieve, and then figure out how I'll achieve that, and that's really about how I manage people, because at the end of the day, I wasn't trained at a company to manage people, so it's all very intentional relative to, these are the types of things we need to do to achieve the goals that we want to achieve, so there's a deep intentionality that increased over the years, for sure, from nothing, literally.

AI assessment note: “I've moved to a much more intentional model”

Q Not at all. I've been wanting to do this one for a long time, but I do want to start with a little bit on you and a bit of the story. 24 years now with Insight, so how did you make your way into the world of Venture, and what was that entry for you?

A Yeah, my story starts, I grew up in Jersey, which I'm in New York City, so it's about 20 miles across the river. My dad's a union electrician. My mom did odd jobs growing up. Neither of my parents graduated college, so we didn't have a lot of money. Total working class. And if you asked me, you know, what venture capital was when I was a teenager, I would have looked at you with a blank, you know, stare in my face. What I did growing up to make some money is work with my dad. So on the weekends and after school, I was his helper. And I'm a small little guy. What that usually meant was I was digging ditches to run wire or working my way through attics pulling wire. And what you learn, and it was probably the number one first life lesson I got, was manual labor isn't fun. I mean, I learned that like the hard way because I was doing it. And I quickly realized I wanted to use my brain, not my brawn, although I didn't have much brawn, to make a living. I started thinking about what do you do to use your brain? My dad's friends were electricians and plumbers and carpenters, so I didn't really know people that had done business or done highly intellectual things. So to me, I had this very narrow set. It was pre-internet. I was either going to be a lawyer, a doctor, or a business person. I didn't like the law shows on TV, so that was out. Doctoring, I was afraid of blood, so that was o…

AI assessment note: “Yeah, my story starts, I grew up in Jersey”

Q But what do you think you do to train them in a way that others don't to make them so good?

A We flipped the notion of investing in venture capital on its head, so if you look back 25 years ago, there weren't Junior people in venture capital is a bunch of senior people. I mean, I got rejected by every one of those senior people, and I sent them resumes from Penn. They didn't take junior people. You needed operating experience. What we did was we said, no, there's a role for junior people. In fact, in a world that's decentralized, in a world that's global, in a world that's innovating very quickly, you need to hire super, super smart, super energetic, super passionate, inquisitive people to go find really interesting stuff, and if it's Command and control and on the bottleneck, we're going to be outdated very quickly. That is the start of kind of the culture and the idea, and that's what we did at the beginning, and we institutionalized that. If you think about learning in general, a very, very simplistic framework, you know, at the one extreme, you have educational institutions, classroom learning, and at the other extreme, you have doing. I would argue in our business, and in most business, classrooms don't work. I mean, I took marketing classes. You know, most Business classes aren't practical relative to what it is to be a VC. I mean, I've taught classes at Columbia and Penn and other places on VC, and it's a hard thing to teach. Like, how do you teach a young person…

AI assessment note: “The Insight approach is all about giving young people actual experience”

Q How do you create a safe environment where young people feel comfortable to challenge, to ask dumb questions, which I always say to my team, there's no such thing as a dumb question, but ask more base questions to challenge you to make mistakes. How do you create that environment of safety without it being soft and cuddly? We're here to work as well.

A It's all about trust. That is what we do, and that's what we do well. That is the core of our culture. It's this notion of Trust. And it was different growing up for me because there's two commodities. I always think about it this way. There's two commodities in life. You have money and you have time. And I had a wise entrepreneur a long time ago say, you can't have both. You have one. You're either long one and short the other or short one and long the other. And in our world at this point, you know, when we were growing up, we had time. We didn't have a lot of money. So like I worked a lot to make a little bit of money. Now I have, I'm long money and I'm short time. So the most precious commodity I have, I'd argue the most precious commodity you have is your time. We give it away pretty freely actually. When people ask us to do stuff, you know, saying no is a pretty important Part of, I think, living that we actually don't respect because if somebody asks us for money, we'd be like, are you crazy? I'm not giving you, you know, a hundred bucks or 500 bucks, but like if somebody asks us for, can I talk to you for five minutes? You're like, okay, how much is your time worth? What we do at Insight is we take that idea of time and trust, and when an analyst joins Insight, they basically have full cart, blanche control of senior partners' calendars, and what I mean by that is if an…

AI assessment note: “when an analyst joins Insight, they basically have full cart, blanche control of senior partners' calendars”

Q purely on the investing side, but it's, it's crucial to everything that we do. It's firm building. It's probably the most challenging of all. 24 years now, you've been in many different positions within Insight, and, you know, for the last several years, been building the firm as one of the leaders. What are some of the biggest challenges of firm building, do you think, from your time building Insight?

A Yeah, you know, we've gone from when I started, there was a couple of us, and, you know, now we have hundreds. So it's all about the people. I think the mission and uniqueness of Insight is we have created an organization, a culture, and a platform that takes very, very talented young people and turns them into world-class software investors and investors And I think that's what we do. I think uniquely well at scale and have done that. So I think our biggest challenge and our biggest opportunity and our biggest differentiation is to continue to do that well. And as you get bigger and bigger, we have amazing ingredients, but we're taking really, really talented young people. And then literally within two to five years, we have these amazing investors and that are literally world-class.

AI assessment note: “our biggest challenge and our biggest opportunity and our biggest differentiation is to continue to do that”

Q Now, I think the big point to consider when we think about pricing is where you sit in the stack. Are you early stage? Are you late stage? Are you pre IPO? Now we're going to hear an incredible perspective from Jeff Lieberman at insight partners.

A I think the most important thing about price, well, two things. One is The only thing we can control ultimately is the quality of an asset that we invest in. So we spend a lot more thinking about the quality of an asset and the future potentiality of the asset. So the way I think about pricing is I go five to seven years out, think about what this business looks like in a base case scenario. And it's not just revenue, it's, it's profit potential. We trick ourselves and just throw revenue multiples around. But at the end of the day, even in the world of SaaS, which is pretty predictable, one SaaS company will have a 20% cashflow margin. One is going to be theoretically in the longterm. This is my Wharton education kicking in two and a half times more valuable than the other. But the point being is I think in markets like this, we value all revenue streams, cashflow streams the same. And ultimately I think that's where the opportunity is, is to focus on things that others don't see relative to quality and pricing of that quality. I think in times like this, we typically average assets get priced way up. Great assets get priced up, but the, the spread between those assets Probably compresses. And then some assets get left behind for no apparent reason too. I think there's opportunities across all that to think through the relative value of the different assets. When you leave SaaS…

AI assessment note: “The only thing we can control ultimately is the quality of an asset”

Q How do you create a safe environment where young people feel comfortable to challenge, to ask dumb questions, which I always say to my team, there's no such thing as a dumb question, but ask more base questions to challenge you to make mistakes. How do you create that environment of safety without it being soft and cuddly? We're here to work as well.

A It's all about trust. That is what we do, and that's what we do well. That is the core of our culture. It's this notion of Trust. And it was different growing up for me because there's two commodities. I always think about it this way. There's two commodities in life. You have money and you have time. And I had a wise entrepreneur a long time ago say, you can't have both. You have one. You're either long one and short the other or short one and long the other. And in our world at this point, you know, when we were growing up, we had time. We didn't have a lot of money. So like I worked a lot to make a little bit of money. Now I have, I'm long money and I'm short time. So the most precious commodity I have, I'd argue the most precious commodity you have is your time. We give it away pretty freely actually. When people ask us to do stuff, you know, saying no is a pretty important Part of, I think, living that we actually don't respect because if somebody asks us for money, we'd be like, are you crazy? I'm not giving you, you know, a hundred bucks or 500 bucks, but like if somebody asks us for, can I talk to you for five minutes? You're like, okay, how much is your time worth? What we do at Insight is we take that idea of time and trust, and when an analyst joins Insight, they basically have full cart, blanche control of senior partners' calendars, and what I mean by that is if an…

AI assessment note: “when an analyst joins Insight, they basically have full cart, blanche control of senior partners' calendars”